The answer to both is yes*
*some of the newer players might need a newish version of the recordbox software to talk properly, such as nexus 2. It really depends on what version you have currently, and what equipment you’re playing on

This. iTunes keeps the folder structure in check based on the metadata. Tech is trends are moving toward less caring about folders, more about metadata, as it’s more efficient. Get on board, or be left in the dust

I got a couple of the NI packs using vouchers I got for free. They had some good sounds.
Haven't purchased off any 3rd party sites. There's heaps of free maschine packs available if you look around a bit. Sometimes tutorials have a pack to download that goes with it containing some samples.
Perhaps even look at getting 1 or 2 3rd party synths and learning them really well. It may be better (from a learning perspective) to do this, rather than buying komplete and using a fraction of it.

NI just unveiled a free software update for Maschine users that introduces the monophonic bass synth and isomorphic keyboard. Maschine 2.6.8 brings some powerful features for all Maschine hardware.
August 22, 2017, Berlin - Native Instruments today releases the MASCHINE 2.6.8 software update, available free for all MASCHINE 2 customers. The update introduces a monophonic bass synth and an isomorphic keyboard.
The new MASCHINE bass synth lets users design and shape rich bass tones with intuitive, fun, and fully-automatable controls directly from the hardware. Users will be able to morph seamlessly from sine to saw to square -- and all spots in between – to create their own unique sounds. They can also load presets designed by professional sound designers to get bass tones for any genre, including booming sub-bass or dripping acid. MASCHINE JAM users can also program the signature glides and accents of classic acid directly from the hardware.
The bass synth does not replace popular products like MASSIVE and MONARK. Instead, it decreases the barrier of entry, allowing users with limited knowledge of synthesis to create beautiful bass tones using the workflow they know with the quality that comes with Native Instruments’ acclaimed DSP expertise.
MASCHINE 2.6.8 also introduces an isomorphic keyboard mode to easily play harmonies and melodies on the MASCHINE JAM 8x8 grid. In this mode, the notes on the keyboard are only the notes from the scale. Additionally, each chord has its own hand shape – regardless of key – so users don’t need to know musical theory to play with perfect pitch. Plus, it’s easier to learn and play than on a traditional piano. Users can easily learn the shape for a chord in one key, and use the same shape in another. A chord guide is available as a free, downloadable PDF to help kickstart the learning process.
MASCHINE 2.6.8 is available free for MASCHINE 2 owners.
Source: https://ask.audio/articles/native-instruments-releases-maschine-268-new-bass-synth-isomorphic-keyboard